Four Chicago Boutique Hotels

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Experience the vibrant spirit of Chicago by choosing from these four outstanding boutique hotels, which offer a unique and unforgettable stay.

I trek up to Chicago often enough. I have been there 3 or 4 times this year, with another one planned soon, primarily for business. Being in St. Louis, Chicago, just North of us is a quick 45-minute flight or a five-hour drive. I’ve stayed at my share of Chicago boutique hotels and your standard cookie-cutter business hotels over the years. I have some favorites that I love and will recommend. But I have also stayed at my share of “eh” hotels, not the exciting, unique hotels I prefer—nothing to write home about, so they’re not on my list.

I have a wish list of hotels that I’d still like to stay, but I often find it challenging due to high prices. When I visit, it’s often for a trade show, and we all know that hotel rates in the city skyrocket during those events. Chicago can be an expensive place to stay!

Here are a few Chicago boutique hotels that have made my list of worthiness. Keep reading to the end to see my wish list of hotels, and let me know if you have additional recommendations for me to stay.

The Gray

122 W. Monroe, Chicago, IL 60603

The Gray is a member of the Kimpton brand of hotels. I am fond of Kimpton Hotels, having stayed with them since before they became part of IHG. I still keep their loyalty card tucked away in my drawer like a cherished keepsake.

Located in the financial district of Chicago, this hotel is elegant and sophisticated with hints of art deco and modern. It is housed in a historic building once the New York Life Insurance Building, which was built in the late 1800s. Its long bank of golden elevators perfectly complements the marble staircase, ceiling, and walls, from which it gets its name from the Georgia Gray marble.

The room was awfully quiet for a hotel room in the middle of a bustling city.

Vol. 39 is the lobby bar, and don’t forget that every Kimpton hotel offers a wine happy hour with complimentary red and white wines. The Gray is no exception.

Cocktail bar Boleo is located on the rooftop. When I visited, the retractable roof was closed, but can you imagine sipping a cocktail in this space with the roof wide open to the sky?

Chicago Athletic Association

12 S Michigan Avenue, Chicago, IL 60603

The Chicago Athletic Association is a fantastic hotel on Michigan Avenue across from Millennium Park. It is part of the World of Hyatt. It used to be a men’s club, and it still keeps that vibe with pommel horses turned benches in the rooms. This gives the place a classy and masculine feel.

The hotel has a rooftop that I visit even when I’m staying elsewhere because it offers fantastic views of the lake and park, along with amazing cocktails. It’s called Cindy’s and has a glass atrium area and an open outside area with views of the lake.

The lobby, which resembles a historical gothic library, is where you can enjoy cocktails, work, read, or simply relax in old-school charm.

Head to the game room if you want to have more fun.

Hotel Lincoln

1816 North Clark Street, Chicago, IL 60614

Hotel Lincoln is in the Lincoln Park area, and you really can’t miss it with that big portrait of President Abraham Lincoln on the side of the building. The neighborhood is super walkable, plus there’s a park right across the street with nice views of the lake. If you’re lucky, you might even catch the farmers market happening in the park. Additionally, it is within walking distance to the Lincoln Park Zoo. Hotel Lincoln is also part of the World of Hyatt hotel brand.

J. Parker Rooftop Bar is a very cool rooftop bar with beautiful lake views. It definitely has a hip vibe, appealing to a younger professional crowd, but it’s not too loud or stuck in one era. I felt comfortable there.

21C Museum Hotel

55 E Ontario St, Chicago, IL 60611

The 21C Museum Hotel brand is one of my favorites, so I was excited when a new location opened in Chicago. Situated in the River North area, this hotel is truly unique, featuring a museum-style art exhibit that is open to the public. The hotel’s signature color is green, which is also reflected in its flock of green plastic penguins. Each 21C Museum Hotel has a distinct set of four-foot-tall penguins created by Cracking Art that wander throughout the hotel. Additionally, each hotel in the 21C brand is distinguished by its own specific color of penguins (St. Louis is orange).

The rooms are modern, sophisticated, and comfortable. You will find original art on the walls, a rubber ducky in the bathroom (or closet), a rain shower, and plenty of outlets for your gadgets. The couch, equipped with USB ports, is perfect for catching up on work emails quickly.

Final Thought

I plan to keep updating this article by adding and removing hotels as I continue to explore the Chicago boutique hotel scene. Hopefully, one of the four hotels listed below will be my next choice for a stay. I also hope you choose one of the above hotels for your next stay and have a great experience. If you have any recommendations I should consider, please let me know! With such a large city, there are many options that I may not be aware of.


Wish List

The Robey

The Peninsula Chicago

Trump International Hotel Chicago

Virgin Hotels Chicago

You may also like these hotels, Five Cool Hotels in Milwaukee with a Historic Building Vibe, A Delafield Hotel To Remember, A Boutique Hotel in Indianapolis, IN, and Hotel Peter and Paul, one of the most unique hotels in New Orleans.

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